Antibacterial and antifungal composition

ABSTRACT

An antibacterial and antifungal composition comprising (A) at least one member selected from the group consisting of dehydroacetic acid, sorbic acid and their alkali metal salts and (B) at least one member selected from the group consisting of o-phenylphenol and its alkali metal salts, p-chloro-m-xylenol, 2-(4-thiazolyl)-1H-benzimidazole, 8-hydroxyquinoline and its salts and chelates, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate, tetrachloroisophthalonitrile and N-(fluorodichloromethylthio)phthalimide. The antibacterial and antifungal effects can be synergistically increased when the component (A) is employed in combination with the component (B).

BACKGROUND OF THE INVENTION

The present invention relates to a composition useful as antibacterialand antifungal agent, and more particularly to a composition mainlycontaining dehydroacetic acid, sorbic acid or their alkali metal salts.

It is well known that dehydroacetic acid, sorbic acid and their alkalimetal salts are useful as antibacterial and antifungal agents. Thetoxicity of these antibacterial and antifungal agents is so low thattheir addition to foods is permitted, and they are agents of very highsafety. Therefore, if these agents are usable in any fields such asgeneral industrial products and agricultural products, to say nothing offoods, the usefulness of these agents becomes very great. However, theantibacterial and antifungal effects thereof are not alwayssatisfactory, and they are restricted in the application to industrialproducts such as paints, sizing agents and adhesives.

SUMMARY OF THE INVENTION

In accordance with the present invention, there is provided anantibacterial and antifungal composition comprising (A) at least onemember selected from the group consisting of dehydroacetic acid, sorbicacid and their alkali metal salts and (B) at least one member selectedfrom the group consisting of o-phenylphenol and its alkali metal salts,p-chloro-m-xylenol, 2-(4-thiazolyl)-1H-benzimidazole, 8-hydroxyquinolineand its salts and chelates, methyl1-(butylcarbamoyl)-2-benzimidazolecarbamate,tetrachloroisophthalonitrile andN-(fluorodichloromethylthio)phthalimide. The synergistic effect on theantibacterial and antifungal properties is very remarkable, when thecomponent (A) is employed in combination with the component (B), and thecomposition of the invention can be availably employed as antibacterialand antifungal agents in various industrial products and agricalturalproducts.

DETAILED DESCRIPTION

There are employed, as the component (A) of the composition of theinvention, dehydroacetic acid, sorbic acid and their alkali metal saltssuch as sodium dehydroacetate, potassium dehydroacetate, sodium sorbateand potassium sorbate. These compounds may be employed alone or inadmixture thereof.

Examples of a compound employed as the component (B) of the compositionof the invention are o-phenylphenol and its alkali metal salts shown bythe following formula: ##STR1## wherein X is hydrogen or an alkalimetal, p-chloro-m-xylenol shown by the following formula: ##STR2##2-(4-thiazolyl)-1H-benzimidazole shown by the following formula:##STR3## 8-hydroxyquinoline shown by the following formula: ##STR4##salts of 8-hydroxyquinoline with organic or inorganic acids such ashydrochloric acid, sulfuric acid and acetic acid, e.g.8-hydroxyquinoline sulfate of the formula: ##STR5## chelates of8-hydroxyquinoline with metals such as copper and zinc, methyl1-(butylcarbamoyl)-2-benzimidazolecarbamate shown by the followingformula: ##STR6## tetrachloroisophthalonitrile shown by the followingformula: ##STR7## and N-(fluorodichloromethylthio)phthalimide shown bythe following formula: ##STR8## These compounds may be employed anone orin admixture thereof.

The components (A) and (B) may be employed in any proportions. Ingeneral, it is desirable to employ the component (B) in an amount of 1%to 40% by weight based on the total weight of the composition, since theparticularly remarkable synergistic effect can be obtained. As statedbefore, the feature of the present invention is that the antibacterialand antifungal effects of dehydroacetic acid, sorbic acid or theiralkali metal salts can be remarkably increased by the combination usewith a slight amount of the component (B). Although the compoundsemployed as the component (B) are known as antibacterial and antifungalagents, it has now been found that synergistic antibacterial andantifungal effect unexpected from a single use of various knownantibacterial and antifungal agents can be obtained, when among knownantibacterial and antifungal agents the component (A) and the component(B) are particularly combined. When the content of the component (B) isless than 1% by weight, sufficient synergistic effect cannot beobtained. Also, even if the component (B) is employed in an amount ofmore than 40% by weight, the synergistic effect is not increased.Further, the compounds employed as the component (B) are relativelyexpensive and also the toxicity is higher than the component (A) and,therefore, the use of the component (B) in an amount of more than 40% byweight not only be uneconomical, but also may impair the low toxicitywhich is the feature of the composition of the present invention.

The adding amount of the composition varies depending on the kind of theproducts to be added. In general, sufficient antibacterial andantifungal effects can be obtained in an amount of 50 to 8,000 p.p.m.

Auxiliary agents such as other bactericides, other fungicides, surfaceactive agents and perfumes may be incorporated in the composition of theinvention, as occasion demands.

The composition of the present invention is applicable to any industrialproducts and agricultural products which require the annihilation or theprevention of propagation of bacteria and fungi, such as paints, sizingagents, petroleum products, plastic moldings, fibers, leathers, woods,paper goods, cosmetics, pharmacuticals, medical appliances, industrialequipments and building materials (putties, fiber boards, particleboards, gypsum boards), fruits, grains and vegetables.

The present invention is more particularly described and explained bymeans of the following Examples, in which all % are by weight unlessotherwise noted.

EXAMPLE 1

A liquid culture medium of pH 7.0 containing 1% of peptone, 1% of meatextract and 0.1% of sodium chloride was prepared and sterilized, and 10ml. portions thereof were poured into L-shaped tubes. After adding aprescribed amount of an antibacterial, antifungal composition consistingof the components (A) and (B) as shown in Table 1 to each tube, 0.1 ml.(number of cells: 5×10⁴ cells/ml.) of an aqueous suspension of bacteriaas shown in Table 1 was added to each tube. The thus prepared cultureliquor contained 5×10² cells per milliliter. The culture was carried outat 37° C. for 48 hours with reciprocal shaking, and the state of thegrowth of bacteria was then observed by measuring the number of cells in1 ml. of the culture liquor.

The results are shown in Table 1.

                                      TABLE 1                                     __________________________________________________________________________                                          Amount of                                      Antibacterial, antifungal composition                                                                        composition                                                                          Number of                                                        (A)/(B)                                                                             added  cells                            Bacteria                                                                             Component (A)                                                                             Component (B)                                                                              by weight                                                                           (p.p.m.)                                                                             (cells/ml.)                      __________________________________________________________________________    Staphylococ-                                                                         Sodium dehydroacetate                                                                     N-(fluorodichloro-                                                                         95/5  500    25 × 10                    cus aureus         methylthio)phthalimide                                                                     95/5  1000    3 × 10                                                    90/10 500    18 × 10                                                    90/10 1000    0                                                               80/20 500    17 × 10                                                    80/20 1000    0                                                               60/40 500     0                                                               100/0 500    19 × 10.sup.5                                              100/0 1000   18 × 10.sup.3                                              0/100 25     11 × 10.sup.8                                              0/100 50     10 × 10.sup.5                                              0/100 100     7 × 10.sup.4                                              0/100 200     6 × 10.sup.2              Staphylococ-                                                                         Potassium sorbate                                                                         N-(fluorodichloro-                                                                         95/5  500    30 × 10                    cus aureus         methylthio)phthalimide                                                                     95/5  1000    6                                                               90/10 500    22 × 10                                                    90/10 1000    0                               Staphylococ-                                                                         Potassium sorbate                                                                         N-(fluorodichloro-                                                                         80/20 500    14 × 10                    cus aureus         metylthio)phthalimide                                                                      80/20 1000    0                                                               60/40 500     0                                                               100/0 500    25 × 10.sup.7                                              100/0 1000    9 × 10.sup.5                                              0/100 25     11 × 10.sup.8                                              0/100 50     10 × 10.sup.5                                              0/100 100     7 × 10.sup.4                                              0/100 200     6 × 10.sup.2              Staphylococ-                                                                         Sorbic acid N-(fluorodichloro-                                                                         95/5  500    25 × 10                    cus aureus         methylthio)phthalimide                                                                     95/5  1000    0                                                               90/10 500    15 × 10                                                    90/10 1000    0                                                               80/20 500     0                                                               60/40 500     0                                                               100/0 500    21 × 10.sup.6                                              100/0 1000    5 × 10.sup.3                                              0/100 25     11 × 10.sup.8              Staphylococ-                                                                         Sorbic acid N-(fluorodichloro-                                                                         0/100 50     10 × 10.sup.5              cus aureus         methylthio)phthalimide                                                                     0/100 100     7 × 10.sup.4                                              0/100 200     6 × 10.sup.2              Bacillus                                                                             Sodium dehydroacetate                                                                     Sodium o-phenylphenolate                                                                   95/5  500     9 × 10                    subtilis                        95/5  1000    7                                                               90/10 500     8 × 10                                                    90/10 1000    0                                                               80/20 500     6 × 10                                                    80/20 1000    0                                                               60/40 500     0                                                               100/0 500    23 × 10.sup.7                                              100/0 1000    9 × 10.sup.4                                              0/100 25      3 × 10.sup.7                                              0/100 50     15 × 10.sup.4                                              0/100 100     6 × 10.sup.3                                              0/100 200     9 × 10                    Bacillus                                                                             Potassium sorbate                                                                         Sodium o-phenylphenolate                                                                   95/5  500    15 × 10                    subtilis                        95/5  1000    2                                                               90/10 500    12 × 10                                                    90/10 1000    1                                                               80/20 500     6 × 10                                                    80/20 1000    0                                                               60/40 500     0                                                               100/0 500     7 × 10.sup.8                                              100/0 1000    5 × 10.sup.7                                              0/100 25      3 × 10.sup.7                                              0/100 50     15 × 10.sup.4                                              0/100 100     6 × 10.sup.3                                              0/100 200     9 × 10                    Bacillus                                                                             Sorbic acid Sodium o-phenylphenolate                                                                   95/5  500    15 × 10                    subtilis                        95/5  1000    0                                                               90/10 500     7 × 10                                                    90/10 1000    0                                                               80/20 500     3 × 10                    Bacillus                                                                             Sorbic acid Sodium o-phenylphenolate                                                                   80/20 1000    0                               subtilis                        60/40 500     0                                                               100/0 500    13 × 10.sup.6                                              100/0 1000   18 × 10.sup.4                                              0/100 25      3 × 10.sup.7                                              0/100 50     15 × 10.sup.4                                              0/100 100     6 × 10.sup.3                                              0/100 200     9 × 10                    Staphylococ-                                                                         Sodium dehydroacetate                                                                     2-(4-Thiazolyl)-1H-                                                                        95/5  500    21 × 10                    cus aureus         benzimidazole                                                                              95/5  1000    6 × 10                                                    90/10 500    20 × 10                                                    90/10 1000    9                                                               80/20 500    19 × 10                                                    80/20 1000    8                                                               60/40 500     8 × 10                                                    60/40 1000    5                                                               100/0 500    19 × 10.sup.5                                              100/0 1000   18 × 10.sup.3              Staphylococ-                                                                         Sodium dehydroacetate                                                                     2-(4-Thiazolyl)-1H-                                                                        0/100 25      4 × 10.sup.9              cus aureus         benzimidazole                                                                              0/100 50      4 × 10.sup.8                                              0/100 100    10 × 10.sup.6                                              0/100 200     5 × 10.sup.4              Staphylococ-                                                                         Potassium sorbate                                                                         2-(4-Thiazolyl)-1H-                                                                        95/5  500    25 × 10                    cus aureus         benzimidazole                                                                              95/5  1000    8 × 10                                                    90/10 500    24 × 10                                                    90/10 1000   15                                                               80/20 500    31 × 10                                                    80/20 1000   15                                                               60/40 500    29 × 10                                                    60/40 1000   10                                                               100/0 500    25 × 10.sup.7                                              100/0 1000    9 × 10.sup.5                                              0/100 25      4 × 10.sup.9                                              0/100 50      4 × 10.sup.8                                              0/100 100    10 × 10.sup.6                                              0/100 200     5 × 10.sup.4              Staphylococ-                                                                         Sorbic acid 2-(4-Thiazolyl)-1H-                                                                        95/5  500    30 × 10.sup.2              cus aureus         benzimidazole                                                                              95/5  1000   15 × 10                                                    90/10 500    41 × 10                                                    90/10 1000   35                                                               80/20 500    17 × 10                                                    80/20 1000   10                                                               60/40 500     6 × 10                                                    60/40 1000    5                                                               100/0 500    21 × 10.sup.6                                              100/0 1000    5 × 10.sup.3                                              0/100 25      4 × 10.sup.9                                              0/100 50      4 × 10.sup.8                                              0/100 100    10 × 10.sup.6                                              0/100 200     5 × 10.sup.4              Staphylococ-                                                                         Sodium dehydroacetate                                                                     Methyl 1-(butylcarba-                                                                      95/5  500    23 × 10                    cus aureus         moyl)-2-benzimidazole-                                                                     95/5  1000    5                                                  carbamate    90/10 500    21 × 10                                                    90/10 1000    0                               Staphylococ-                                                                         Sodium dehydroacetate                                                                     Methyl 1-(butylcarba-                                                                      80/20 500    20 × 10                    cus aureus         moyl)-2-benzimidazole-                                                                     80/20 1000    0                                                  carbamate    60/40 500     0                                                               100/0 500    19 × 10.sup.5                                              100/0 1000   18 × 10.sup.3                                              0/100 25      7 × 10.sup.6                                              0/100 50      9 × 10.sup.4                                              0/100 100    12 × 10.sup.2                                              0/100 200     5 × 10                    Staphylococ-                                                                         Potassium sorbate                                                                         Methyl 1-(butylcarba-                                                                      95/5  500    32 × 10                    cus aureus         moyl)-2-benzimidazole-                                                                     95/5  1000   10 × 10                                       carbamate    90/10 500    19 × 10                                                    90/10 1000    0                                                               80/20 500    28 × 10                                                    80/20 1000    0                                                               60/40 500     0                                                               100/0 500    25 × 10.sup.7                                              100/0 1000    9 × 10.sup.5              Staphylococ-                                                                         Potassium sorbate                                                                         Methyl 1-(butylcarba-                                                                      0/100 25      7 × 10.sup.6              cus aureus         moyl)-2-benzimidazole-                                                                     0/100 50      9 × 10.sup.4                                 carbamate    0/100 100    12 × 10.sup.2                                              0/100 200     5 × 10                    Staphylococ-                                                                         Dehydroacetate                                                                            Methyl 1-(butylcarba-                                                                      95/5  500    30 × 10                    cus aureus         moyl)-2-benzimidazole-                                                                     95/5  1000    9 × 10                                       carbamate    90/10 500    15 × 10                                                    90/10 1000    0                                                               80/20 500    15 × 10                                                    80/20 1000    0                                                               60/40 500     0                                                               100/0 500    22 × 10.sup.5                                              100/0 1000    6 × 10.sup.3                                              0/100 25      7 × 10.sup.6                                              0/100 50      9 × 10.sup.4                                              0/100 100    12 × 10.sup.2                                              0/100 200     5 × 10                    Escherichia                                                                          Sodium dehydroacetate                                                                     Tetrachloroisophthalo-                                                                     95/5  500      9                              coli               nitrile      95/5  1000    0                                                               90/10 500     0                                                               80/20 500     0                                                               60/40 500     0                                                               100/0 500     7 × 10.sup.8                                              100/0 1000    9 × 10.sup.7                                              0/100 25      2 × 10.sup.5                                              0/100 50      9 × 10.sup.4                                              0/100 100     7 × 10.sup.2                                              0/100 200     3 × 10                    Escherichia                                                                          Potassium sorbate                                                                         Tetrachloroisophthalo-                                                                     95/5  500    25                               coli               nitrile      95/5  1000    0                                                               90/10 500     0                                                               80/20 500     0                                                               60/40 500     0                                                               100/0 500     6 × 10.sup.9                                              100/0 1000   12 × 10.sup.7              Escherichia                                                                          Potassium sorbate                                                                         Tetrachloroisophthalo-                                                                     0/100 25      2 × 10.sup.5              coli               nitrile      0/100 50      9 × 10.sup.4                                              0/100 100     7 × 10.sup.2                                              0/100 200     3 × 10                     Escherichia                                                                         Dehydroacetic acid                                                                        Tetrachloroisophthalo-                                                                     95/5  500    15                               coli               nitrile      95/5  1000    0                                                               90/10 500     0                                                               80/20 500     0                                                               60/40 500     0                                                               100/0 500    13 × 10.sup.8                                              100/0 1000   31 × 10.sup.6                                              0/100 25      2 × 10.sup.5                                              0/100 50      9 × 10.sup.4                                              0/100 100     7 × 10.sup.2                                              0/100 200     3 × 10                    Pseudomonas                                                                          Sodium dehydroacetate                                                                     8-Hydroxyquinoline                                                                         95/5  500     9 × 10                    aeruginosa         sulfate      95/5  1000    0                                                               90/10 500     5 × 10                                                    90/10 1000    0                                                               80/20 500     8 × 10                                                    80/20 1000    0                                                               60/40 500     40 × 10                                                   60/40 1000    0                                                               100/0 500    15 × 10.sup.8                                              100/0 1000    2 × 10.sup.7                                              0/100 25     22 × 10.sup.6                                              0/100 50     21 × 10.sup.4                                              0/100 100    15 × 10.sup.2                                              0/100 200     4 × 10                    Pseudomonas                                                                          Potassium sorbate                                                                         8-Hydroxyquinoline                                                                         95/5  500    18 × 10                    aeruginosa         sulfate      95/5  1000    4                                                               90/10 500    16 × 10                                                    90/10 1000    0                               Pseudomonas                                                                          Potassium sorbate                                                                         8-Hydroxyquinoline                                                                         80/20 500    17 × 10                    aeruginosa         sulfate      80/20 1000    0                                                               60/40 500    16 × 10                                                    60/40 1000    0                                                               100/0 500    15 × 10.sup.10                                             100/0 1000    7 × 10.sup.8                                              0/100 25     22 × 10.sup.6                                              0/100 50     21 × 10.sup.4                                              0/100 100    15 × 10.sup.2                                              0/100 200     4 × 10                    Pseudomonas                                                                          Sorbic acid 8-Hydroxyquinoline                                                                         95/5  500    19 × 10                    aeruginosa         sulfate      95/5  1000   10                                                               90/10 500    21 × 10                                                    90/10 1000    8                                                               80/20 500    17 × 10                                                    80/20 1000    0                                                               60/40 500    14 × 10                                                    60/40 1000    0                               Pseudomonas                                                                          Sorbic acid 8-Hydroxyquinoline                                                                         100/0 500     9 × 10.sup.9              aeruginosa         sulfate      100/0 1000    8 × 10.sup.7                                              0/100 25     22 × 10.sup.6                                              0/100 50     21 × 10.sup.4                                              0/100 100    15 × 10.sup.2                                              0/100 200     4 × 10                    Pseudomonas                                                                          Sodium dehydroacetate                                                                     p-Chloro-m-xylenol                                                                         95/5  500    15 × 10                    aeruginosa                      95/5  1000    0                                                               90/10 500    13 × 10                                                    90/10 1000    0                                                               80/20 500    12 × 10                                                    80/20 1000    0                                                               60/40 500     0                                                               100/0 500    15 × 10.sup.8                                              100/0 1000    2 × 10.sup.7                                              0/100 25      8 × 10.sup.9                                              0/100 50     15 × 10.sup.6                                              0/100 100    18 × 10.sup. 4                                             0/100 200    13 ×10.sup.2               Pseudomonas                                                                          Potassium sorbate                                                                         p-Chloro-m-xylenol                                                                         95/5  500    20 × 10                    aeruginosa                      95/5  1000    7                                                               90/10 500    17 × 10                                                    90/10 1000    5                                                               80/20 500    15 × 10                                                    80/20 1000    5                                                               60/40 500     3 × 10                                                    60/40 1000    0                                                               100/0 500    15 × 10.sup.10                                             100/0 1000    7 × 10.sup.8                                              0/100 25      8 × 10.sup.9                                              0/100 50     15 × 10.sup.6                                              0/100 100    18 × 10.sup.4                                              0/100 200    13 × 10.sup.2              Pseudomonas                                                                          Sorbic acid p-Chloro-m-xylenol                                                                         95/5  500    18 × 10                    aeruginosa                      95/5  1000    5                                                               90/10 500    10 × 10                                                    90/10 1000    0                                                               80/20 500     9 × 10                                                    80/20 1000    0                                                               60/40 500     0                                                               100/0 500     9 × 10.sup.9                                              100/0 1000    8 × 10.sup.7                                              0/100 25      8 × 10.sup.9                                              0/100 50     15 × 10.sup.6                                              0/100 100    18 × 10.sup.4                                              0/100 200    13 × 10.sup.2              __________________________________________________________________________

EXAMPLE 2

A 5% aqueous solution of starch was prepared and sterilized, and 100 ml.portions thereof were poured into 200 ml. bottles. After adding aprescribed amount of an antibacterial, antifungal composition consistingof the components (A) and (B) as shown in Table 2 to each bottle andthoroughly agitating, 1 ml. (number of fungi: 5×10⁶ fungi/ml.) of anaqueous suspension of fungi as shown in Table 2 was added to each bottleand was agitated again. The thus prepared aqueous solution contained5×10⁴ fungi per gram. The bottles were then sealed and allowed to standat 30° C. for a week. The state of the growth of fungi was observed bymeasuring the number of fungi in 1 g. of the aqueous solution.

The results are shown in Table 2.

                                      TABLE 2                                     __________________________________________________________________________                                          Amount of                                      Antibacterial, antifungal composition                                                                        composition                                                                          Number of                                                        (A)/(B)                                                                             added  fungi                            Fungi  Component (A)                                                                             Component (B)                                                                              by weight                                                                           (p.p.m.)                                                                             (fungi/g.)                       __________________________________________________________________________    Trichoderma                                                                          Sodium dehydroacetate                                                                     N-(fluorodichloro-                                                                         95/5  100     4 × 10                    viride             methylthio)phthalimide                                                                     95/5  500     0                                                               90/10 100     2 × 10                                                    90/10 500     0                                                               80/20 100     8                                                               80/20 500     0                                                               60/40 100     0                                                               100/0 100    29 × 10.sup.8                                              100/0 500    34 × 10.sup.5                                              0/100 5       7 × 10.sup.7                                              0/100 25     16 × 10.sup.6                                              0/100 50     33 × 10.sup.4                                              0/100 100     5 × 10.sup.2              Trichoderma                                                                          Potassium sorbate                                                                         N-(fluorodichloro-                                                                         95/5  100     8 × 10                    viride             methylthio)phthalimide                                                                     95/5  500     0                                                               90/10 100     5 × 10                                                    90/10 500     0                                                               80/20 100     7                               Trichoderma                                                                          Potassium sorbate                                                                         N-(fluorodichloro-                                                                         80/20 500     0                               viride             methylthio)phthalimide                                                                     60/40 100     0                                                               100/0 100    27 × 10.sup.10                                             100/0 500     9 × 10.sup.8                                              0/100 5       7 × 10.sup.7                                              0/100 25     16 × 10.sup.6                                              0/100 50     33 × 10.sup.4                                              0/100 100     5 × 10.sup.2              Trichoderma                                                                          Dehydroacetic acid                                                                        N-(fluorodichloro-                                                                         95/5  100     3 × 10                    viride             methylthio)phthalimide                                                                     95/5  500     0                                                               90/10 100     0                                                               80/20 100     0                                                               60/40 100     0                                                               100/0 100    25 × 10.sup.8                                              100/0 500    30 × 10.sup.5                                              0/100 5       7 × 10.sup.7                                              0/100 25     16 × 10.sup.6                                              0/100 50     33 × 10.sup.4              Trichoderma                                                                          Dehydroacetic acid                                                                        N-(fluorodichloro-                                                                         0/100 100     5 × 10.sup.2              viride             methylthio)phthalimide                                     Cladosporium                                                                         Sodium dehydroacetate                                                                     Sodium o-phenylphenolate                                                                   95/5  500     8 × 10                    resinae                         95/5  1000    5                                                               90/10 500     5                                                               90/10 1000    0                                                               80/20 500     5                                                               80/20 1000    0                                                               60/40 500     0                                                               100/0 500    31 × 10.sup.6                                              100/0 1000   28 × 10.sup.3                                              0/100 25      8 × 10.sup.10                                             0/100 50     18 × 10.sup.8                                              0/100 100    34 × 10.sup.6                                              0/100 200     5 × 10                    Cladosporium                                                                         Potassium sorbate                                                                         Sodium o-phenylphenolate                                                                   95/5  500    15 × 10                    resinae                         95/5  1000    3                                                               90/10 500    10 × 10                    Cladosporium                                                                         Potassium sorbate                                                                         Sodium o-phenylphenolate                                                                   90/10 1000    0                               resinae                         80/20 500     9                                                               80/20 1000    0                                                               60/40 500     0                                                               100/0 500    13 × 10.sup.6                                              100/0 1000   25 × 10.sup.3                                              0/100 25      8 × 10.sup.10                                             0/100 50     18 × 10.sup.8                                              0/100 100    34 × 10.sup.6                                              0/100 200     5 × 10                    Cladosporium                                                                         Dehydroacetic acid                                                                        Sodium o-phenylphenolate                                                                   95/5  500     7 × 10                    resinae                         95/5  1000    0                                                               90/10 500     4                                                               90/10 1000    0                                                               80/20 500     0                                                               60/40 500     0                                                               100/0 500    10 × 10.sup.5                                              100/0 1000    9 × 10.sup.3              Cladosporium                                                                         Dehydroacetic acid                                                                        Sodium o-phenylphenolate                                                                   0/100 25      8 × 10.sup.10             resinae                         0/100 50     18 × 10.sup.8                                              0/100 100    34 × 10.sup.6                                              0/100 200     5 × 10                    Aspergillus                                                                          Sodium dehydroacetate                                                                     2-(4-Thiazolyl)-1H-                                                                        95/5  500     7 × 10                    niger              benzimidazole                                                                              95/5  1000    0                                                               90/10 500     0                                                               80/20 500     0                                                               60/40 500     0                                                               100/0 500    18 ×  10.sup.10                                            100/0 1000   30 × 10.sup.4                                              0/100 25     37 × 10.sup.8                                              0/100 50     18 × 10.sup.5                                              0/100 100    11 × 10.sup.3                                              0/100 200     4 × 10                    Aspergillus                                                                          Potassium sorbate                                                                         2-(4-Thiazolyl)-1H-                                                                        95/5  500    21 × 10                    niger              benzimidazole                                                                              95/5  1000    3                                                               90/10 500     3 × 10                                                    90/10 1000    0                                                               80/20 500     0                                                               60/40 500     0                                                               100/0 500     7 × 10.sup.10                                             100/0 1000   37 × 10.sup.8                                              0/100 25     37 × 10.sup.8                                              0/100 50     18 × 10.sup.5                                              0/100 100    11 × 10.sup.3                                              0/100 200     4 × 10                    Aspergillus                                                                          Dehydroacetic acid                                                                        2-(4-Thiazolyl)-1H-                                                                        95/5  500     5 × 10                    niger              benzimidazole                                                                              95/5  1000    0                                                               90/10 500     0                                                               80/20 500     0                                                               60/40 500     0                                                               100/0 500    17 × 10.sup.10             Aspergillus                                                                          Dehydroacetic acid                                                                        2-(4-Thiazolyl)-1H-                                                                        100/0 1000   25 × 10.sup.4              niger              benzimidazole                                                                              0/100 25     37 × 10.sup.8                                              0/100 50     18 × 10.sup.5                                              0/100 100    11 × 10.sup.3                                              0/100 200     4 × 10                    Penicillium                                                                          Sodium dehydroacetate                                                                     Methyl 1-(butylcarba-                                      citrinum           moyl)-2-benzimidazole-                                                                     95/5  500    23 × 10                                       carbamate    95/5  1000    8                                                               90/10 500     2 × 10                                                    90/10 1000    0                                                               80/20 5000    5                                                               80/20 1000    0                                                               60/40 500     0                                                               100/0 500    17 × 10.sup.5                                              100/0 1000   35 × 10.sup.4                                              0/100 25     13 × 10.sup.8                                              0/100 50     19 × 10.sup.6                                              0/100 100     9 × 10.sup.3                                              0/100 200     3 × 10                    Penicillium                                                                          Potassium sorbate                                                                         Methyl 1-(butylcarba-                                      citrinum           moyl)-2-benzimidazole-                                                                     95/5  500    19 × 10                                       carbamate    95/5  1000    9                                                               90/10 500    10 × 10                                                    90/10 1000    1                                                               80/20 500     7                                                               80/20 1000    0                                                               60/40 500     0                                                               100/0 500     4 × 10.sup.9                                              100/0 1000   12 × 10.sup.7                                              0/100 25     13 × 10.sup.8                                              0/100 50     19 × 10.sup.6                                              0/100 100     9 × 10.sup.3                                              0/100 200     3 × 10                    Penicillium                                                                          Sorbic acid Methyl 1-(butylcarba-                                      citrinum           moyl)-2-benzimidazole-                                                                     95/5  500     8 × 10                                       carbamate    95/5  1000    5                                                               90/10 500     5 × 10                                                    90/10 1000    2                               Penicillium                                                                          Sorbic acid Methyl 1-(butylcarba-                                      citrinum           moyl)-2-benzimidazole-                                                                     80/20 500     0                                                  carbamate    60/40 500     0                                                               100/0 500     7 × 10.sup.7                                              100/0 1000   40 × 10.sup.5                                              0/100 25     13 × 10.sup.8                                              0/100 50     19 × 10.sup.6                                              0/100 100     9 × 10.sup.3                                              0/100 200     3 × 10                    Aspergillus                                                                          Sodium dehydroacetate                                                                     Tetrachloroisophthalo-                                                                     95/5  100     2                               niger              nitrile      95/5  500     0                                                               90/10 100     0                                                               80/20 100     0                                                               60/40 100     0                                                               100/0 100    25 × 10.sup.10                                             100/0 500    18 × 10.sup.7                                              0/100 5       7 × 10.sup.4                                              0/100 25      8 × 10.sup.3                                              0/100 50      3 × 10                    Aspergillus                                                                          Potassium sorbate                                                                         Tetrachloroisophthalo-                                                                     95/5  100    13 × 10                    niger              nitrile      95/5  500     0                                                               90/10 100     0                                                               80/20 100     0                                                               60/40 100     0                                                               100/0 100    33 × 10.sup.11                                             100/0 500     7 × 10.sup.10                                             0/100 5       7 × 10.sup.4                                              0/100 25      8 × 10.sup.3                                              0/100 50      3 × 10                    Aspergillus                                                                          Sorbic acid Tetrachloroisophthalo-                                                                     95/5  100    10× 10                     niger              nitrile      95/5  500     0                                                               90/10 100     0                                                               80/20 100     0                                                               60/40 100     0                                                               100/0 100    32 × 10.sup.10                                             100/0 500     5 × 10.sup.9              Aspergillus                                                                          Sorbic acid Tetrachloroisophthalo-                                                                     0/100 5       7 × 10.sup.4              niger              nitrile      0/100 25      8 × 10.sup.3                                              0/100 50      3 × 10                    Aspergillus                                                                          Sodium dehydroacetate                                                                     8-Hydroxyquinoline                                                                         95/5  500     3                               niger              sulfate      95/5  1000    0                                                               90/10 500     2                                                               90/10 1000    0                                                               80/20 500     0                                                               60/40 500     0                                                               100/0 500    18 × 10.sup.7                                              100/0 1000   30 × 10.sup.4                                              0/100 25     10 × 10.sup.6                                              0/100 50      7 × 10.sup. 3                                             0/100 100     6 × 10.sup.2                                              0/100 200     6 × 10                    Aspergillus                                                                          Potassium sorbate                                                                         8-Hydroxyquinoline                                                                         95/5  500    13 × 10                    niger              sulfate      95/5  1000    0                                                               90/10 500     8                                                               90/10 1000    0                                                               80/20 500     0                                                               60/40 500     0                                                               100/0 500     7 × 10.sup.10                                             100/0 1000   37 × 10.sup.8                                              0/100 25     10 × 10.sup.6                                              0/100 50      7 × 10.sup.3                                              0/100 100     6 × 10.sup.2                                              0/100 200     6 × 10                    Aspergillus                                                                          Dehydroacetic acid                                                                        8-Hydroxyquinoline                                                                         95/5  500     2                               niger              sulfate      95/5  1000    0                                                               90/10 500     2                                                               90/10 1000    0                                                               80/20 500     0                                                               60/40 500     0                               Aspergillus                                                                          Dehydroacetic acid                                                                        8-Hydroxyquinoline                                                                         100/0 500    10 × 10.sup.7              niger              sulfate      100/0 1000   25 × 10.sup.4                                              0/100 25     10 × 10.sup.6                                              0/100 50      7 × 10.sup.3                                              0/100 100     6 × 10.sup.2                                              0/100 200     6 × 10                    Aspergillus                                                                          Sodium dehydroacetate                                                                     p-Chloro-m-xylenol                                                                         95/5  500    10 × 10                    niger                           95/5  1000    0                                                               90/10 500     0                                                               80/20 500     0                                                               60/40 500     0                                                               100/0 500    18 × 10.sup.7                                              100/0 1000   30 × 10.sup.4                                              0/100 25     14 × 10.sup.9                                              0/100 50     16 × 10.sup.6                                              0/100 100    12 × 10.sup.4                                              0/100 200     5 × 10                    Aspergillus                                                                          Potassium sorbate                                                                         p-Chloro-m-xylenol                                                                         95/5  500    15 × 10                    niger                           95/5  1000    0                                                               90/10 500     5 × 10                                                    90/10 1000    0                                                               80/20 500     0                                                               60/40 500     0                                                               100/0 500     7 ×  10.sup.10                                            100/0 1000   37 × 10.sup.8                                              0/100 25     14 × 10.sup.9                                              0/100 50     16 × 10.sup.6                                              0/100 100    12 × 10.sup.4                                              0/100 200     5 × 10                    Aspergillus                                                                          Dehydroacetic acid                                                                        p-Chloro-m-xylenol                                                                         95/5  500     6 × 10                    niger                           95/5  1000    0                                                               90/10 500     0                                                               80/20 500     0                                                               60/40 500     0                                                               100/0 500    10 × 10.sup.7              Aspergillus                                                                          Dehydroacetic acid                                                                        p-Chloro-m-xylenol                                                                         100/0 1000   25 × 10.sup.4              niger                           0/100 25     14 × 10.sup.9                                              0/100 50     16 × 10.sup.6                                              0/100 100    12 × 10.sup.4                                              0/100 200     5 × 10                    __________________________________________________________________________

EXAMPLE 3

A 2% of aqueous solution of carboxymethyl cellulose was prepared andadjusted to pH 7. After adding antibacterial, antifungal compositionconsisting of the components (A) and (B) to the solution in aconcentration as shown in Table 3, a slight amount of a putridcarboxymethyl cellulose was added to the solution. The solution wasstored in an air-conditioned room at 37° C. and the putrefraction of thesolution was obserbed with the lapse of time.

The results are shown in Table 3, in which symbols are as follows:

-: No putrefaction

+: Putrefaction

                                      TABLE 3                                     __________________________________________________________________________    Antibacterial, antifungal composition                                                     Concent-          Concent-                                                                           Time elapsed                                           ration            ration                                                                             After                                                                             After                                                                              After                             Component (A)                                                                             (p.p.m.)                                                                           Component (B)                                                                              (p.p.m.)                                                                           1 week                                                                            2 weeks                                                                            3 weeks                           __________________________________________________________________________    Sodium dehydroacetate                                                                     500  Sodium o-phenylphenolate                                                                   10   -   -    -                                 Potassium sorbate                                                                         500  Sodium o-phenylphenolate                                                                   50   -   -    -                                 --          0    Sodium o-phenylphenolate                                                                   100  -   +    +                                 Sodium dehydroacetate                                                                     2000 --           0    -   -    +                                 Potassium sorbate                                                                         2000 --           0    -   +    +                                 --          0    --           0    +   +    +                                 __________________________________________________________________________

EXAMPLE 4

An antibacterial, antifungal composition was added to a 6% aqueoussolution of glue in a concentration as shown in Table 4. The solutionwas stored in an air-conditioned room at 50° C. and the decrease of theviscosity due to putrefaction was observed with the lapse of time.

The results are shown in Table 4, in which symbols are as follows:

-: No decrease of viscosity

+: Decrease of viscosity

                                      TABLE 4                                     __________________________________________________________________________    Antibacterial, antifungal composition                                                     Concent-          Concent-                                                                           Time elapsed                                           ration            ration                                                                             After                                                                             After                                                                              After                             Component (A)                                                                             (p.p.m.)                                                                           Component (B)                                                                              (p.p.m.)                                                                           1 week                                                                            2 weeks                                                                            3 weeks                           __________________________________________________________________________    Sodium dehydroacetate                                                                     1000 Sodium o-phenylphenolate                                                                   50   -   -    -                                 Potassium sorbate                                                                         2000 Sodium o-phenylphenolate                                                                   50   -   -    -                                 --          0    Sodium o-phenylphenolate                                                                   200  +   +    +                                 Sodium dehydroacetate                                                                     5000 --           0    -   -    +                                 Potassium sorbate                                                                         5000 --           0    -   -    +                                 --          0    --           0    +   +    +                                 __________________________________________________________________________

EXAMPLE 5

An antibacterial, antifungal composition was added to an ethylene-vinylacetate copolymer emulsion containing polyvinyl alcohol as an emulsifierin a concentration as shown in Table 5. A slight amount of a putridemulsion was added to the emulsion and the number of cells wasimmediately measured. The emulsion was then stored in an air-conditionedroom at 30° C., and after 3 weeks, the number of cells in the emulsionwas measured again to determine the preservative and fungicidal effects.

The results are shown in Table 5.

                                      TABLE 5                                     __________________________________________________________________________    Antibacterial, antifungal composition                                                 Concent-     Concent-                                                                           Number of cells (cell/g.)                                   ration       ration                                                                             Before storage After 3 weeks                        Component (A)                                                                         (p.p.m.)                                                                           Component (B)                                                                         (p.p.m.)                                                                           Fungi                                                                              Yeast                                                                              Bacteria                                                                           Fungi                                                                              Yeast                                                                              Bacteria                   __________________________________________________________________________    Potassium de-                                                                              Sodium o-phe-                                                    hydroacetate                                                                          3000 nylphenolate                                                                          100  51 × 10.sup.6                                                                15 × 10.sup.6                                                                7 × 10.sup.3                                                                 <10.sup.2                                                                          <10.sup.2                                                                          2 × 10.sup.2         Potassium    Sodium o-phe-                                                    sorbate 4000 nylphenolate                                                                          200  35 × 10.sup.6                                                                19 × 10.sup.6                                                                5 × 10.sup.3                                                                 <10.sup.2                                                                          <10.sup.2                                                                          4 × 10.sup.2         --           Sodium o-phe-                                                            0    nylphenolate                                                                          1000 25 × 10.sup.6                                                                19 × 10.sup.6                                                                9 × 10.sup.3                                                                 31 × 10.sup.5                                                                22 × 10.sup.5                                                                9 × 10.sup.3         Sodium de-                                                                            5000 --                                                               hydroacetate         0    30 ×  10.sup.6                                                               26 × 10.sup.6                                                                6 × 10.sup.3                                                                 72 × 10.sup.4                                                                18 × 10.sup.4                                                                6 × 10.sup.3         Potassium    --                                                               sorbate 5000         0    17 × 10.sup.6                                                                24 × 10.sup.6                                                                6 × 10.sup.3                                                                 10 × 10.sup.6                                                                29 × 10.sup.5                                                                5 × 10.sup.3         --      0    --      0    51 × 10.sup.6                                                                18 × 10.sup.6                                                                8 × 10.sup.3                                                                 23 × 10.sup.7                                                                25 × 10.sup.6                                                                8 × 10.sup.3         __________________________________________________________________________

EXAMPLE 6

A 10% aqueous solution of a polyvinly alcohol sizing agent was preparedand divided into three portions. To the first portion was added nomedicine, to the second portion was added 2,000 p.p.m. of sodiumdehydroacetate, and to the third portion were added 1,000 p.p.m. ofsodium dehydroacetate and 100 p.p.m. of p-chloro-m-xylenol. Epicoccumsp. was inoculated to each of the three portions, and they were placedin an incubator at 30° C. and allowed to stand for 14 days.

In the first and second portions, development of fungi was observedafter 3 and 5 days, respectively, but in the third portion nodevelopment of fungi was observed.

The above procedure was repeated except that, as the component (B),2-(4-thiazolyl)-1H-benzimidazole, 8-hydroxyquinoline sulfate, methyl1-(butylcarbamoyl)-2-benzimidazolecarbamate,tetrachloroisophthalonitrile or N-(fluorodichloromethylthio)phthalimidewas employed instead of p-chloro-m-xylenol. The same results as abovewere obtained with respect to all the above compounds.

EXAMPLE 7

The procedures of Example 6 were repeated except that potassium sorbatewas employed instead of sodium dehydroacetate.

With respect to all tests using six components (B) in Example 6, in thefirst and second portions development of fungi was observed after 4 to 6days, respectively, but in the third portion no development of fungi wasobserved.

EXAMPLE 8

An antibacterial, antifungal composition was prepared by admixing 95 g.of sodium dehydroacetate as the component (A) and 5 g. of the component(B) shown in Table 6. The composition was added to a 18% solution of acrotonic acid-vinyl acetate copolymer in a concentration of 2,500p.p.m., 5,000 p.p.m. or 7,500 p.p.m. to give three kinds of the coatingsolutions.

Each solution was sprayed onto two sides of a fancy mat (10×10 cm.) inan amount of 2 g. on each side, and was then dried at 140° C. for 2minutes.

The coated fancy mats were allowed to stand under a saturated humidityat 25° C., and the state of the growth of fungi was observed with thelapse of time.

The results are shown in Table 6, in which symbols are as follows:

-: No growth

±: A little growth

+: Growth (The more the number of the symbol +, the larger the growth.)

                                      TABLE 6                                     __________________________________________________________________________                     Concentration                                                                 of composition                                                                        Days elapsed                                         Component (B)    (p.p.m.)                                                                              5 6 7  8   10   12    14                             __________________________________________________________________________    p-Chloro-m-xylenol                                                                             0       - - +  ++  +++  +++++ +++++                                           2500    - - ±                                                                             +   +++  +++   ++++                                            5000    - - -  ±                                                                              +    ++    +++                                             7500    - - -  -   -    -     -                              2-(4-Thiazolyl)-1H-benzimidazole                                                               0       - + ++ +++ ++++ +++++ +++++                                           2500    - - +  +   +++  +++   ++++                                            5000    - - -  ±                                                                              +    ++    +++                                             7500    - - -  -   -    -     -                              8-Hydroxyquinoline sulfate                                                                     0       - + ++ +++ ++++ +++++ +++++                                           2500    - - +  +   +++  +++   ++++                                            5000    - - -  ±                                                                              +    ++    +++                                             7500    - - -  -   -    -     -                              Methyl 1-(butylcarbamoyl)-2-benz-                                                              0       - + ++ +++ ++++ +++++ +++++                          imidazolecarbamate                                                            2500             -       - + +  +++ +++  ++++                                                  5000    - - -  ±                                                                              +    ++    +++                                             7500    - - -  -   -    -     -                              Tetrachloroisophthalonitrile                                                                   0       - + ++ + ++                                                                              ++++ +++++ +++++                                           2500    - - ±                                                                             +   +++  +++   ++++                                            5000    - - -  -   ± +     ++                                              7500    - - -  -   -    -     -                              N-(fluorodichloromethylthio)-                                                                  0       - + ++ +++ ++++ +++++ +++++                          phthalimide      2500    - ±                                                                            +  +   +++  +++   ++++                                            5000    - - -  ±                                                                              +    ++    +++                                             7500    - - -  -   -    -     -                              __________________________________________________________________________

EXAMPLE 9

A sizing solution containing 5% of wheat starch and a sizing solutioncontaining 5% of casein were prepared, and thereto was added anantibacterial or antifungal agent as shown in Table 7. After adding asuspension of fungi consisting of Aspergillus niger, Penicilliumcitrinum, Cladosporium herbaum and Chaetomium globosum to each of thesizing solutions, the sizing solutions were placed in an incubator at28° C. and the state of the growth of fungi was observed with the lapseof time.

The results are shown in Table 7, in which symbols are as follows:

-: No growth

±: A little growth

+: Growth (The more the number of the symbol +, the larger the growth.)

                                      TABLE 7                                     __________________________________________________________________________    Sizing                       Incubation days                                  solution                                                                             Antibacterial, antifungal agent                                                                     0 4 7   14   21   28                             __________________________________________________________________________    Wheat starch                                                                         None                  - + +++ ++++ ++++ ++++                           Casein "                     - - ++  +++  ++++ ++++                           Wheat starch                                                                         Sodium dehydroacetate (500 p.p.m.)                                                                  - - ±                                                                              ++   +++  +++                            Casein "                     - - -   +    ++   +++                            Wheat starch                                                                         Sodium dehydroacetate (475 p.p.m.) and                                        p-Chloro-m-xylenol (25 p.p.m.)                                                                      - - -   -    -    -                              Casein Sodium dehydroacetate (475 p.p.m.) and                                                              - - -   -    -    --                                    p-Chloro-m-xylenol (25 p.p.m.)                                         Wheat starch                                                                         Sodium dehydroacetate (475 p.p.m.) and                                                              - - -   -    -    -                                     2-(4-Thiazolyl)-1H-benzimidazole (25 p.p.m.)                           Casein Sodium dehydroacetate (475 p.p.m.) and                                                              - - -   -    -    -                                     2-(4-Thiazolyl)-1H-benzimidazole (25 p.p.m.)                           Wheat starch                                                                         Sodium dehydroacetate (475 p.p.m.) and                                                              - - -   -    -    -                                     8-Hydroxyquinoline sulfate (25 p.p.m.) -Casein                                                      Sodium dehydroacetate (475 p.p.m.)                                              -nd                                                                             -   -    -    - -                                   8-Hydroxyquinoline sulfate (25 p.p.m.)                                 Wheat starch                                                                         Sodium dehydroacetate (475 p.p.m.) and                                                              - - -   -    -    -                                     Methyl 1-(butylcarbamoyl)-2-benzimidazole-                                    carbamate (25 p.p.m.)                                                  Casein Sodium dehydroacetate (475 p.p.m.) and                                                              - - -   -    -    -                                     Methyl 1-(butylcarbamyl)-2-benzimidazole                                      carbamate (25 p.p.m.)                                                  Wheat starch                                                                         Sodium dehydroacetate (475 p.p.m.) and                                                              - - -   -    -    -                                     Tetrachloroisophthalonitrile (25 p.p.m.)                               Casein Sodium dehydroacetate (475 p.p.m.) and                                                              - - -   -    -    -                                     Tetrachloroisophthalonitrile (25 p.p.m.)                                      Sodium dehydroacetate (475 p.p.m.) and                                 Wheat starch                                                                         N-(fluorodichloromethylthio)phthalimide                                                             - - -   -    -    -                                     (25 p.p.m.)                                                            Casein Sodium dehydroacetate (475 p.p.m.) and                                                              - - -   -    -    -                                     N-(fluorodichloromethylthio)phthalimide                                       (25 p.p.m.)                                                            __________________________________________________________________________

What we claim is:
 1. An antibacterial and antifungal compositioncomprising a mixture of:(A) at least one member selected from the groupconsisting of dehydroacetic acid, and its alkali metal salts, whereinsaid member is contained within said composition in an amount 60-95% byweight, based on the total weight of the composition, and (B)tetrachloroisophthalonitrile in a synergistically effective amount offrom 1% to 40% by weight based on the total weight of the composition.2. An antibacterial and antifungal composition as in claim 1, whereinsaid tetrachloroisophthalonitrile is contained within said compositionin an amount of from 5% to 40% by weight based on the total weight ofthe composition.